We, the smartphone-and-MP3-addicted people, wear headphones from dusk till dawn. That means they've got to be comfortable for hours on end. Forget the bulk of fashion-forward full-sized cans and the irritation of earbuds—for headphones that go the distance, three qualities trump everything else: comfort, durability, practicality.

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We tested five pairs of on-ear headphones, all weighing less than three ounces and costing less than $105 on Amazon. Sound quality is always important, but like the slick gadgets you plug them into, headphones should fit effortlessly into your life. If you're going to take these everywhere and wear them constantly, they've got to look good and stow away easily. Of course, these headphones all borrow something of the Walkman-chic style of the 1980s, so if they're aesthetically covetable, we're not going to complain.

5th Place: Aiaiai Tracks

The Tracks' unassuming looks centers around the split-design of the stainless steel headband, doubling as the mechanism to adjust the earphones. (Note: you must complete the assembly of Tracks after you buy them.) This makes the headphones beautiful, unique, and completely impractical, considering the headphones tend to fall apart in a bag. While that steel is undeniably tough, adjusting the headphones to your head isn't a smooth slide, but rough like locking the hinges on a folding table. What's worse, the beauty doesn't last; the headphones come in a painted matte finish that almost immediately started chipping off.

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The Tracks are designed to be seen, but unlike some of the very good Aiaiai products we've tested, the Tracks are better off unheard. They sound budget—almost like you're wearing your computer's built-in speakers on your ears. On the plus side, they've got a nice blend of lows and highs and handle hip hop well enough. But overall the Tracks sound harsh, compressed, and if we didn't know better, we'd say the bursty, bright highs sound distorted.

4th Place: Koss Porta Pro KTC

The Porta Pros were originally designed over 25 years ago, and Koss recently updated the headphones for the 21st century by adding an iPhone remote. But how does the sound hold up a quarter-century later? Pretty darn well, actually. They handle deep, hip-hop bass lines beautifully, and pack a punch on thick, layered rock music. These are great for all around listening, but when you compare them to some of the newer headphones in this test, they tend sound subdued and bland because there's no umph in the mids to bring out the character of your music.

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As you'd expect, the 1980s design looks wonderfully retro now. The Porta Pros are very comfortable. The earphones tilt every which way to match the shape of your ears, and the flexible metal band doesn't pinch your head or grab your hair at all. There's even a little switch-like slider on each ear, which allows you to choose how firm you want the fit. When it's time to put them away, the Porta Pros fold into an easy-to-carry package that's more pocketable than the rest. Still, for all the benefits of the old design, the Porta Pros feel cheap and flimsy. Sure, they held up during our test, but you get the feeling that if dropped, they'd be done for.

3rd Place: Bang & Olufsen Form 2

The Form 2's sturdy plastic headband is impressive and fashionable; the headphones could easily double as a bold accessory to keep a carefully coiffed bob in place. The rigid band flexes in all the right ways to fit your head, but that these headphones are comfortable at all owes to the tiltable, foam-padded phones which swivel into place on your ears. Any while they hold firmly onto your head, but the pressure causes an irritating itchiness. And sadly, they don't so much fold up. Fashion bends to no one, it seems.

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When it comes to performance, however, the Form 2s sound great. They're immersive, detailed, and do a great job of representing the space and depth of recordings. They're versatile cans, emphasizing just the right tonal frequencies no matter what music you're listening to. And though the bass is sufficient, the Form 2s definitely err on the side of mids and highs.

2nd Place: Jays v-Jays

The v-Jays are the comfort champions. They're the lightest headphones in this Battlemodo, to the point that you sometimes forget you're wearing them. A bulk of the v-Jays' weight is contained on the rectangular, plush earphones, which are gently clamped to your head by a thin plastic band. They sit perfectly. You'll wear them all day and basically forget that they're there. From the design point of view, our only quibble is that they fold, but only partially.

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And wow, v-Jays can seriously push air. The headphones deliver rich bass, and generally excellent sound across tonal frequencies. They'll do you well for any music which prominently features a kick drum or heavy bass line. The v-Jays have nice detail and resolution, but you're definitely giving up a little in the area of nuance for their powerful, full sound.

BESTMODO!! Sennheiser PX 100-II

Every detail has been attended to on the PX 100-IIs. The headphones fold into a slim compact package. Their build is sturdy. Though the earphones are only lightly-foamed, they're not the least bit irritating. Sennheiser even tossed in some soft padding at the hinges of the headband for extra comfort.

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Oh, and they sound spectacular. The PX 100-II's deliver lovely, textured bass of the kind you'd expect from much more expensive headphones. But what's really impressive is that the PX 100-II sound full-bodied without losing a bit of detail from the music. You get everything: A dizzying sense of depth and space as well as tiny nuances like the unique shimmer of different cymbals or the slight change in delay speed on a guitar accent. Delicious.